This invention relates to a novel process for preparing 2-haloethylamides by the reaction of 2-oxazolidinone and an appropriate acid halide.
The 2-haloethylamides prepared according to the invention are useful chemical intermediates for preparation of herbicides and other biologically active compounds and photographic products. It is previously known to prepare the 2-haloethylamides by the reaction of ethyleneimine with suitable acid halides. Examples include the reaction of simple carboxylic acid chlorides, A. H. Bestian, Justus Liebigs Ann. Chem., 566, 210 (1950); chloroformates, A. Seeger, Justus Liebigs Ann. Chem., 575, 153 (1962); and sulfonyl chlorides, C. W. Marckwald et al., Ber., 34, 3544 (1901). Generally, excess acid halide is required in order to minimize polymerization, e.g., polyaminoethylation reactions. Additionally, the toxicity of ethyleneimine reduces the utility of these prior art processes. An alternative route to these useful chemical intermediates would therefore be desirable.